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Elizabeth H Jeffery - One of the best experts on this subject based on the ideXlab platform.
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Influence of Seasonal Variation and Methyl Jasmonate Mediated Induction of Glucosinolate Biosynthesis on Quinone Reductase Activity in Broccoli Florets
2016Co-Authors: Elizabeth H Jeffery, John A JuvikAbstract:Methyl jasmonate spray treatments (250 μM) were utilized to alter glucosinolate composition in the florets of the commercial broccoli F1 hybrids ‘Pirate’, ‘Expo’, ‘Green Magic’, ‘Imperial’, and ‘Gypsy’ grown in replicated field plantings in 2009 and 2010. MeJA treatment significantly increased glucoraphanin (11%), gluconasturtiin (59%), and neoglucobrassicin (248%) concentrations and their hydrolysis products including Sulforaphane (152%), phenethyl isothiocyanate (318%), N-methoxyindole-3-carbinol (313%), and neoascorbigen (232%) extracted from florets of these genotypes over two seasons. Increased quinone reductase (QR) activity was significantly correlated with increased levels of Sulforaphane, N-methoxyindole-3-carbinol, and neoascorbigen. Partitioning experiment-wide trait variances indicated that the variability in concentrations of Sulforaphane (29%), neoascorbigen (48%), and QR activity (72%) was influenced by year-associated weather variables, whereas variation in neoglucobrassicin (63%) and N-methoxyindole-3-carbinol (46%) concentrations was primarily attributed to methyl jasmonate treatment. These results suggest that methyl jasmonate treatment can enhance QR inducing activity by increased hydrolysis of glucoraphanin into Sulforaphane and the hydrolysis products of neoglucobrassicin
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exogenous methyl jasmonate treatment increases glucosinolate biosynthesis and quinone reductase activity in kale leaf tissue
PLOS ONE, 2014Co-Authors: Elizabeth H Jeffery, John A JuvikAbstract:Methyl jasmonate (MeJA) spray treatments were applied to the kale varieties ‘Dwarf Blue Curled Vates’ and ‘Red Winter’ in replicated field plantings in 2010 and 2011 to investigate alteration of glucosinolate (GS) composition in harvested leaf tissue. Aqueous solutions of 250 µM MeJA were sprayed to saturation on aerial plant tissues four days prior to harvest at commercial maturity. The MeJA treatment significantly increased gluconasturtiin (56%), glucobrassicin (98%), and neoglucobrassicin (150%) concentrations in the apical leaf tissue of these genotypes over two seasons. Induction of quinone reductase (QR) activity, a biomarker for anti-carcinogenesis, was significantly increased by the extracts from the leaf tissue of these two cultivars. Extracts of apical leaf tissues had greater MeJA mediated increases in phenolics, glucosinolate concentrations, GS hydrolysis products, and QR activity than extracts from basal leaf tissue samples. The concentration of the hydrolysis product of glucoraphanin, sulforphane was significantly increased in apical leaf tissue of the cultivar ‘Red Winter’ in both 2010 and 2011. There was interaction between exogenous MeJA treatment and environmental conditions to induce endogenous JA. Correlation analysis revealed that indole-3-carbanol (I3C) generated from the hydrolysis of glucobrassicin significantly correlated with QR activity (r = 0.800, P<0.001). Concentrations required to double the specific QR activity (CD values) of I3C was calculated at 230 µM, which is considerably weaker at induction than other isothiocyanates like sulforphane. To confirm relationships between GS hydrolysis products and QR activity, a range of concentrations of MeJA sprays were applied to kale leaf tissues of both cultivars in 2011. Correlation analysis of these results indicated that Sulforaphane, NI3C, neoascorbigen, I3C, and diindolylmethane were all significantly correlated with QR activity. Thus, increased QR activity may be due to combined increases in phenolics (quercetin and kaempferol) and GS hydrolysis product concentrations rather than by individual products alone.
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glucosinolate hydrolysis and bioavailability of resulting isothiocyanates focus on glucoraphanin
Journal of Functional Foods, 2014Co-Authors: Donato Angelino, Elizabeth H JefferyAbstract:There is a growing interest in the health benefits of broccoli. Sulforaphane, the major bioactive component in broccoli, is an unstable isothiocyanate stored in the plant as glucoraphanin. Myrosinase enzymes release Sulforaphane when the plant is crushed. Extraction during supplement formulation or heat processing can destroy myrosinase. When myrosinase activity is lost, colonic microbiota perform this hydrolysis in vivo. Here we review hydrolysis by myrosinase and microbiota. Myrosinase acts fast to generate a bolus of SF that is rapidly absorbed high in the gut and rapidly excreted. Microbial metabolism is slow and delayed. Sulforaphane absorption, distribution and excretion are discussed.
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impact of thermal processing on Sulforaphane yield from broccoli brassica oleracea l ssp italica
Journal of Agricultural and Food Chemistry, 2012Co-Authors: Grace C Wang, Mark W Farnham, Elizabeth H JefferyAbstract:In broccoli, Sulforaphane forms when the glucosinolate glucoraphanin is hydrolyzed by the endogenous plant thiohydrolase myrosinase. A myrosinase cofactor directs hydrolysis away from the formation of bioactive Sulforaphane and toward an inactive product, Sulforaphane nitrile. The cofactor is more heat sensitive than myrosinase, presenting an opportunity to preferentially direct hydrolysis toward Sulforaphane formation through regulation of thermal processing. Four broccoli cultivars were microwave heated, boiled, or steamed for various lengths of time. Production of nitrile during hydrolysis of unheated broccoli varied among cultivars from 91 to 52% of hydrolysis products (Pinnacle > Marathon > Patriot > Brigadier). Boiling and microwave heating caused an initial loss of nitrile, with a concomitant increase in Sulforaphane, followed by loss of Sulforaphane, all within 1 min. In contrast, steaming enhanced Sulforaphane yield between 1.0 and 3.0 min in all but Brigadier. These data are proof of concept tha...
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epithiospecifier protein from broccoli brassica oleracea l ssp italica inhibits formation of the anticancer agent Sulforaphane
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nathan V Matusheski, Richard Mithen, John A Juvik, Ranjan Swarup, Malcolm J Bennett, Elizabeth H JefferyAbstract:In some cruciferous plants, epithiospecifier protein (ESP) directs myrosinase (EC 3.2.3.1)-catalyzed hydrolysis of alkenyl glucosinolates toward epithionitrile formation. Here, for the first time, we show that ESP activity is negatively correlated with the extent of formation of the health-promoting phytochemical Sulforaphane in broccoli (Brassica oleracea L. ssp. italica). A 43 kDa protein with ESP activity and sequence homology to the ESP of Arabidopsis thaliana was cloned from the broccoli cv. Packman and expressed in Escherichia coli. In a model system, the recombinant protein not only directed myrosinase-dependent metabolism of the alkenyl glucosinolate epi-progoitrin [(2S)-2-hydroxy-3-butenyl glucosinolate] toward formation of an epithionitrile but also directed myrosinase-dependent hydrolysis of the glucosinolate glucoraphanin [4-(methylsulfinyl)butyl glucosinolate] to form Sulforaphane nitrile, in place of the isothiocyanate Sulforaphane. The importance of this finding is that, whereas sulforaphan...
Jed W Fahey - One of the best experts on this subject based on the ideXlab platform.
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biomarker exploration in human peripheral blood mononuclear cells for monitoring Sulforaphane treatment responses in autism spectrum disorder
Scientific Reports, 2020Co-Authors: Andrew W Zimmerman, Katherine K Stephenson, Albena T Dinkovakostova, Kanwaljit Singh, Susan L Connors, Eileen Diggins, Jed W FaheyAbstract:Autism Spectrum Disorder (ASD) is one of the most common neurodevelopmental disorders with no drugs treating the core symptoms and no validated biomarkers for clinical use. The multi-functional phytochemical Sulforaphane affects many of the biochemical abnormalities associated with ASD. We investigated potential molecular markers from three ASD-associated physiological pathways that can be affected by Sulforaphane: redox metabolism/oxidative stress; heat shock response; and immune dysregulation/inflammation, in peripheral blood mononuclear cells (PBMCs) from healthy donors and patients with ASD. We first analyzed the mRNA levels of selected molecular markers in response to Sulforaphane ex vivo treatment in PBMCs from healthy donors by real-time quantitative PCR. All of the tested markers showed quantifiability, accuracy and reproducibility. We then compared the expression levels of those markers in PBMCs taken from ASD patients in response to orally-delivered Sulforaphane. The mRNA levels of cytoprotective enzymes (NQO1, HO-1, AKR1C1), and heat shock proteins (HSP27 and HSP70), increased. Conversely, mRNA levels of pro-inflammatory markers (IL-6, IL-1β, COX-2 and TNF-α) decreased. Individually none is sufficiently specific or sensitive, but when grouped by function as two panels, these biomarkers show promise for monitoring pharmacodynamic responses to Sulforaphane in both healthy and autistic humans, and providing guidance for biomedical interventions.
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keap1 and done targeting the nrf2 pathway with Sulforaphane
Trends in Food Science and Technology, 2017Co-Authors: Jed W Fahey, Thomas W Kensler, Albena T Dinkovakostova, Rumen V KostovAbstract:Abstract Background Since the re-discovery of Sulforaphane in 1992 and the recognition of the bioactivity of this phytochemical, many studies have examined its mode of action in cells, animals and humans. Broccoli, especially as young sprouts, is a rich source of Sulforaphane and broccoli-based preparations are now used in clinical studies probing efficacy in health preservation and disease mitigation. Many putative cellular targets are affected by Sulforaphane although only one, KEAP1-NRF2 signaling, can be considered a validated target at this time. The transcription factor NRF2 is a master regulator of cell survival responses to endogenous and exogenous stressors. Scope and Approach This review summarizes the chemical biology of Sulforaphane as an inducer of NRF2 signaling and efficacy as an inhibitor of carcinogenesis. It also provides a summary of the current findings from clinical trials using a suite of broccoli sprout preparations on a series of short-term endpoints reflecting a diversity of molecular actions. Key Findings and Conclusions Sulforaphane, as a pure chemical, protects against chemical-induced skin, oral, stomach, colon, lung and bladder carcinogenesis and in genetic models of colon and prostate carcinogenesis. In many of these settings the antitumorigenic efficacy of Sulforaphane is dampened in Nrf2-disrupted animals. Broccoli preparations rich in glucoraphanin or Sulforaphane exert demonstrable pharmacodynamic action in over a score of clinical trials. Measures of NRF2 pathway response and function are serving as guideposts for the optimization of dose, schedule and formulation as clinical trials with broccoli-based preparations become more commonplace and more rigorous in design and implementation.
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prevention of carcinogen induced oral cancer by Sulforaphane
Cancer Prevention Research, 2016Co-Authors: Julie E Bauman, Yan Zang, Malabika Sen, Lin Wang, Patricia A Egner, Jed W Fahey, Daniel P Normolle, Jennifer R Grandis, Thomas W Kensler, Daniel E JohnsonAbstract:Chronic exposure to carcinogens represents the major risk factor for head and neck squamous cell carcinoma (HNSCC). Beverages derived from broccoli sprout extracts (BSE) that are rich in glucoraphanin and its bioactive metabolite Sulforaphane promote detoxication of airborne pollutants in humans. Herein, we investigated the potential chemopreventive activity of Sulforaphane using in vitro models of normal and malignant mucosal epithelial cells and an in vivo model of murine oral cancer resulting from the carcinogen 4-nitroquinoline-1-oxide (4NQO). Sulforaphane treatment of Het-1A, a normal mucosal epithelial cell line, and 4 HNSCC cell lines led to dose- and time-dependent induction of NRF2 and the NRF2 target genes NQO1 and GCLC, known mediators of carcinogen detoxication. Sulforaphane also promoted NRF2-independent dephosphorylation/inactivation of pSTAT3, a key oncogenic factor in HNSCC. Compared with vehicle, Sulforaphane significantly reduced the incidence and size of 4NQO-induced tongue tumors in mice. A pilot clinical trial in 10 healthy volunteers evaluated the bioavailability and pharmacodynamic activity of three different BSE regimens, based upon urinary Sulforaphane metabolites and NQO1 transcripts in buccal scrapings, respectively. Ingestion of Sulforaphane-rich BSE demonstrated the greatest, most consistent bioavailability. Mucosal bioactivity, defined as 2-fold or greater upregulation of NQO1 mRNA, was observed in 6 of 9 evaluable participants ingesting glucoraphanin-rich BSE; 3 of 6 ingesting Sulforaphane-rich BSE; and 3 of 9 after topical-only exposure to Sulforaphane-rich BSE. Together, our findings demonstrate preclinical chemopreventive activity of Sulforaphane against carcinogen-induced oral cancer, and support further mechanistic and clinical investigation of Sulforaphane as a chemopreventive agent against tobacco-related HNSCC. Cancer Prev Res; 9(7); 547-57. ©2016 AACR.
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Sulforaphane bioavailability from glucoraphanin rich broccoli control by active endogenous myrosinase
PLOS ONE, 2015Co-Authors: Paul Talalay, Jed W Fahey, David W Holtzclaw, Scott L Wehage, Kristina L Wade, Katherine K StephensonAbstract:Glucoraphanin from broccoli and its sprouts and seeds is a water soluble and relatively inert precursor of Sulforaphane, the reactive isothiocyanate that potently inhibits neoplastic cellular processes and prevents a number of disease states. Sulforaphane is difficult to deliver in an enriched and stable form for purposes of direct human consumption. We have focused upon evaluating the bioavailability of Sulforaphane, either by direct administration of glucoraphanin (a glucosinolate, or β-thioglucoside-N-hydroxysulfate), or by co-administering glucoraphanin and the enzyme myrosinase to catalyze its conversion to Sulforaphane at economic, reproducible and sustainable yields. We show that following administration of glucoraphanin in a commercially prepared dietary supplement to a small number of human volunteers, the volunteers had equivalent output of Sulforaphane metabolites in their urine to that which they produced when given an equimolar dose of glucoraphanin in a simple boiled and lyophilized extract of broccoli sprouts. Furthermore, when either broccoli sprouts or seeds are administered directly to subjects without prior extraction and consequent inactivation of endogenous myrosinase, regardless of the delivery matrix or dose, the Sulforaphane in those preparations is 3- to 4-fold more bioavailable than Sulforaphane from glucoraphanin delivered without active plant myrosinase. These data expand upon earlier reports of inter- and intra-individual variability, when glucoraphanin was delivered in either teas, juices, or gelatin capsules, and they confirm that a variety of delivery matrices may be equally suitable for glucoraphanin supplementation (e.g. fruit juices, water, or various types of capsules and tablets).
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Sulforaphane treatment of autism spectrum disorder asd
Proceedings of the National Academy of Sciences of the United States of America, 2014Co-Authors: Paul Talalay, Jed W Fahey, Kanwaljit Singh, Susan L Connors, Eric A Macklin, Kirby D Smith, Andrew W ZimmermanAbstract:Abstract Autism spectrum disorder (ASD), characterized by both impaired communication and social interaction, and by stereotypic behavior, affects about 1 in 68, predominantly males. The medico-economic burdens of ASD are enormous, and no recognized treatment targets the core features of ASD. In a placebo-controlled, double-blind, randomized trial, young men (aged 13–27) with moderate to severe ASD received the phytochemical Sulforaphane (n = 29)—derived from broccoli sprout extracts—or indistinguishable placebo (n = 15). The effects on behavior of daily oral doses of Sulforaphane (50–150 µmol) for 18 wk, followed by 4 wk without treatment, were quantified by three widely accepted behavioral measures completed by parents/caregivers and physicians: the Aberrant Behavior Checklist (ABC), Social Responsiveness Scale (SRS), and Clinical Global Impression Improvement Scale (CGI-I). Initial scores for ABC and SRS were closely matched for participants assigned to placebo and Sulforaphane. After 18 wk, participants receiving placebo experienced minimal change (<3.3%), whereas those receiving Sulforaphane showed substantial declines (improvement of behavior): 34% for ABC (P < 0.001, comparing treatments) and 17% for SRS scores (P = 0.017). On CGI-I, a significantly greater number of participants receiving Sulforaphane had improvement in social interaction, abnormal behavior, and verbal communication (P = 0.015–0.007). Upon discontinuation of Sulforaphane, total scores on all scales rose toward pretreatment levels. Dietary Sulforaphane, of recognized low toxicity, was selected for its capacity to reverse abnormalities that have been associated with ASD, including oxidative stress and lower antioxidant capacity, depressed glutathione synthesis, reduced mitochondrial function and oxidative phosphorylation, increased lipid peroxidation, and neuroinflammmation.
Nathan V Matusheski - One of the best experts on this subject based on the ideXlab platform.
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epithiospecifier protein from broccoli brassica oleracea l ssp italica inhibits formation of the anticancer agent Sulforaphane
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nathan V Matusheski, Richard Mithen, John A Juvik, Ranjan Swarup, Malcolm J Bennett, Elizabeth H JefferyAbstract:In some cruciferous plants, epithiospecifier protein (ESP) directs myrosinase (EC 3.2.3.1)-catalyzed hydrolysis of alkenyl glucosinolates toward epithionitrile formation. Here, for the first time, we show that ESP activity is negatively correlated with the extent of formation of the health-promoting phytochemical Sulforaphane in broccoli (Brassica oleracea L. ssp. italica). A 43 kDa protein with ESP activity and sequence homology to the ESP of Arabidopsis thaliana was cloned from the broccoli cv. Packman and expressed in Escherichia coli. In a model system, the recombinant protein not only directed myrosinase-dependent metabolism of the alkenyl glucosinolate epi-progoitrin [(2S)-2-hydroxy-3-butenyl glucosinolate] toward formation of an epithionitrile but also directed myrosinase-dependent hydrolysis of the glucosinolate glucoraphanin [4-(methylsulfinyl)butyl glucosinolate] to form Sulforaphane nitrile, in place of the isothiocyanate Sulforaphane. The importance of this finding is that, whereas sulforaphan...
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epithiospecifier protein from broccoli brassica oleracea l ssp italica inhibits formation of the anticancer agent Sulforaphane
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nathan V Matusheski, Richard Mithen, John A Juvik, Ranjan Swarup, Malcolm J Bennett, Elizabeth H JefferyAbstract:In some cruciferous plants, epithiospecifier protein (ESP) directs myrosinase (EC 3.2.3.1)-catalyzed hydrolysis of alkenyl glucosinolates toward epithionitrile formation. Here, for the first time, we show that ESP activity is negatively correlated with the extent of formation of the health-promoting phytochemical Sulforaphane in broccoli (Brassica oleracea L. ssp. italica). A 43 kDa protein with ESP activity and sequence homology to the ESP of Arabidopsis thaliana was cloned from the broccoli cv. Packman and expressed in Escherichia coli. In a model system, the recombinant protein not only directed myrosinase-dependent metabolism of the alkenyl glucosinolate epi-progoitrin [(2S)-2-hydroxy-3-butenyl glucosinolate] toward formation of an epithionitrile but also directed myrosinase-dependent hydrolysis of the glucosinolate glucoraphanin [4-(methylsulfinyl)butyl glucosinolate] to form Sulforaphane nitrile, in place of the isothiocyanate Sulforaphane. The importance of this finding is that, whereas Sulforaphane has been shown to have anticarcinogenic properties, Sulforaphane nitrile has not. Genetic manipulation designed to attenuate or eliminate expression of ESP in broccoli could increase the fractional conversion of glucoraphanin to Sulforaphane, enhancing potential health benefits.
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heating decreases epithiospecifier protein activity and increases Sulforaphane formation in broccoli
Phytochemistry, 2004Co-Authors: Nathan V Matusheski, John A Juvik, Elizabeth H JefferyAbstract:Sulforaphane, an isothiocyanate from broccoli, is one of the most potent food-derived anticarcinogens. This compound is not present in the intact vegetable, rather it is formed from its glucosinolate precursor, glucoraphanin, by the action of myrosinase, a thioglucosidase enzyme, when broccoli tissue is crushed or chewed. However, a number of studies have demonstrated that Sulforaphane yield from glucoraphanin is low, and that a non-bioactive nitrile analog, Sulforaphane nitrile, is the primary hydrolysis product when plant tissue is crushed at room temperature. Recent evidence suggests that in Arabidopsis, nitrile formation from glucosinolates is controlled by a heat-sensitive protein, epithiospecifier protein (ESP), a non-catalytic cofactor of myrosinase. Our objectives were to examine the effects of heating broccoli florets and sprouts on Sulforaphane and Sulforaphane nitrile formation, to determine if broccoli contains ESP activity, then to correlate heat-dependent changes in ESP activity, Sulforaphane content and bioactivity, as measured by induction of the phase II detoxification enzyme quinone reductase (QR) in cell culture. Heating fresh broccoli florets or broccoli sprouts to 60 °C prior to homogenization simultaneously increased Sulforaphane formation and decreased Sulforaphane nitrile formation. A significant loss of ESP activity paralleled the decrease in Sulforaphane nitrile formation. Heating to 70 °C and above decreased the formation of both products in broccoli florets, but not in broccoli sprouts. The induction of QR in cultured mouse hepatoma Hepa lclc7 cells paralleled increases in Sulforaphane formation.
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heating decreases epithiospecifier protein activity and increases Sulforaphane formation in broccoli
Phytochemistry, 2004Co-Authors: Nathan V Matusheski, John A Juvik, Elizabeth H JefferyAbstract:Sulforaphane, an isothiocyanate from broccoli, is one of the most potent food-derived anticarcinogens. This compound is not present in the intact vegetable, rather it is formed from its glucosinolate precursor, glucoraphanin, by the action of myrosinase, a thioglucosidase enzyme, when broccoli tissue is crushed or chewed. However, a number of studies have demonstrated that Sulforaphane yield from glucoraphanin is low, and that a non-bioactive nitrile analog, Sulforaphane nitrile, is the primary hydrolysis product when plant tissue is crushed at room temperature. Recent evidence suggests that in Arabidopsis, nitrile formation from glucosinolates is controlled by a heat-sensitive protein, epithiospecifier protein (ESP), a non-catalytic cofactor of myrosinase. Our objectives were to examine the effects of heating broccoli florets and sprouts on Sulforaphane and Sulforaphane nitrile formation, to determine if broccoli contains ESP activity, then to correlate heat-dependent changes in ESP activity, Sulforaphane content and bioactivity, as measured by induction of the phase II detoxification enzyme quinone reductase (QR) in cell culture. Heating fresh broccoli florets or broccoli sprouts to 60 °C prior to homogenization simultaneously increased Sulforaphane formation and decreased Sulforaphane nitrile formation. A significant loss of ESP activity paralleled the decrease in Sulforaphane nitrile formation. Heating to 70 °C and above decreased the formation of both products in broccoli florets, but not in broccoli sprouts. The induction of QR in cultured mouse hepatoma Hepa lclc7 cells paralleled increases in Sulforaphane formation.
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preparative hplc method for the purification of Sulforaphane and Sulforaphane nitrile from brassica oleracea
Journal of Agricultural and Food Chemistry, 2001Co-Authors: Nathan V Matusheski, John A Juvik, Matthew A Wallig, Barbara P Klein, Mosbah M Kushad, Elizabeth H JefferyAbstract:An extraction and preparative HPLC method has been devised to simultaneously purify Sulforaphane and Sulforaphane nitrile from the seed of Brassica oleracea var. italica cv. Brigadier. The seed was defatted with hexane, dried, and hydrolyzed in deionized water (1:9) for 8 h. The hydrolyzed seed meal was salted and extracted with methylene chloride. The dried residue was redissolved in a 5% acetonitrile solution and washed with excess hexane to remove nonpolar contaminants. The aqueous phase was filtered through a 0.22-microm cellulose filter and separated by HPLC using a Waters Prep Nova-Pak HR C-18 reverse-phase column. Refractive index was used to detect Sulforaphane nitrile, and absorbance at 254 nm was used to detect Sulforaphane. Peak identification was confirmed using gas chromatography and electron-impact mass spectrometry. Each kilogram of extracted seed yielded approximately 4.8 g of Sulforaphane and 3.8 g of Sulforaphane nitrile. Standard curves were developed using the purified compounds to allow quantification of Sulforaphane and Sulforaphane nitrile in broccoli tissue using a rapid GC method. The methodology was used to compare Sulforaphane and Sulforaphane nitrile content of autolyzed samples of several broccoli varieties.
John A Juvik - One of the best experts on this subject based on the ideXlab platform.
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Influence of Seasonal Variation and Methyl Jasmonate Mediated Induction of Glucosinolate Biosynthesis on Quinone Reductase Activity in Broccoli Florets
2016Co-Authors: Elizabeth H Jeffery, John A JuvikAbstract:Methyl jasmonate spray treatments (250 μM) were utilized to alter glucosinolate composition in the florets of the commercial broccoli F1 hybrids ‘Pirate’, ‘Expo’, ‘Green Magic’, ‘Imperial’, and ‘Gypsy’ grown in replicated field plantings in 2009 and 2010. MeJA treatment significantly increased glucoraphanin (11%), gluconasturtiin (59%), and neoglucobrassicin (248%) concentrations and their hydrolysis products including Sulforaphane (152%), phenethyl isothiocyanate (318%), N-methoxyindole-3-carbinol (313%), and neoascorbigen (232%) extracted from florets of these genotypes over two seasons. Increased quinone reductase (QR) activity was significantly correlated with increased levels of Sulforaphane, N-methoxyindole-3-carbinol, and neoascorbigen. Partitioning experiment-wide trait variances indicated that the variability in concentrations of Sulforaphane (29%), neoascorbigen (48%), and QR activity (72%) was influenced by year-associated weather variables, whereas variation in neoglucobrassicin (63%) and N-methoxyindole-3-carbinol (46%) concentrations was primarily attributed to methyl jasmonate treatment. These results suggest that methyl jasmonate treatment can enhance QR inducing activity by increased hydrolysis of glucoraphanin into Sulforaphane and the hydrolysis products of neoglucobrassicin
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exogenous methyl jasmonate treatment increases glucosinolate biosynthesis and quinone reductase activity in kale leaf tissue
PLOS ONE, 2014Co-Authors: Elizabeth H Jeffery, John A JuvikAbstract:Methyl jasmonate (MeJA) spray treatments were applied to the kale varieties ‘Dwarf Blue Curled Vates’ and ‘Red Winter’ in replicated field plantings in 2010 and 2011 to investigate alteration of glucosinolate (GS) composition in harvested leaf tissue. Aqueous solutions of 250 µM MeJA were sprayed to saturation on aerial plant tissues four days prior to harvest at commercial maturity. The MeJA treatment significantly increased gluconasturtiin (56%), glucobrassicin (98%), and neoglucobrassicin (150%) concentrations in the apical leaf tissue of these genotypes over two seasons. Induction of quinone reductase (QR) activity, a biomarker for anti-carcinogenesis, was significantly increased by the extracts from the leaf tissue of these two cultivars. Extracts of apical leaf tissues had greater MeJA mediated increases in phenolics, glucosinolate concentrations, GS hydrolysis products, and QR activity than extracts from basal leaf tissue samples. The concentration of the hydrolysis product of glucoraphanin, sulforphane was significantly increased in apical leaf tissue of the cultivar ‘Red Winter’ in both 2010 and 2011. There was interaction between exogenous MeJA treatment and environmental conditions to induce endogenous JA. Correlation analysis revealed that indole-3-carbanol (I3C) generated from the hydrolysis of glucobrassicin significantly correlated with QR activity (r = 0.800, P<0.001). Concentrations required to double the specific QR activity (CD values) of I3C was calculated at 230 µM, which is considerably weaker at induction than other isothiocyanates like sulforphane. To confirm relationships between GS hydrolysis products and QR activity, a range of concentrations of MeJA sprays were applied to kale leaf tissues of both cultivars in 2011. Correlation analysis of these results indicated that Sulforaphane, NI3C, neoascorbigen, I3C, and diindolylmethane were all significantly correlated with QR activity. Thus, increased QR activity may be due to combined increases in phenolics (quercetin and kaempferol) and GS hydrolysis product concentrations rather than by individual products alone.
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epithiospecifier protein from broccoli brassica oleracea l ssp italica inhibits formation of the anticancer agent Sulforaphane
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nathan V Matusheski, Richard Mithen, John A Juvik, Ranjan Swarup, Malcolm J Bennett, Elizabeth H JefferyAbstract:In some cruciferous plants, epithiospecifier protein (ESP) directs myrosinase (EC 3.2.3.1)-catalyzed hydrolysis of alkenyl glucosinolates toward epithionitrile formation. Here, for the first time, we show that ESP activity is negatively correlated with the extent of formation of the health-promoting phytochemical Sulforaphane in broccoli (Brassica oleracea L. ssp. italica). A 43 kDa protein with ESP activity and sequence homology to the ESP of Arabidopsis thaliana was cloned from the broccoli cv. Packman and expressed in Escherichia coli. In a model system, the recombinant protein not only directed myrosinase-dependent metabolism of the alkenyl glucosinolate epi-progoitrin [(2S)-2-hydroxy-3-butenyl glucosinolate] toward formation of an epithionitrile but also directed myrosinase-dependent hydrolysis of the glucosinolate glucoraphanin [4-(methylsulfinyl)butyl glucosinolate] to form Sulforaphane nitrile, in place of the isothiocyanate Sulforaphane. The importance of this finding is that, whereas sulforaphan...
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epithiospecifier protein from broccoli brassica oleracea l ssp italica inhibits formation of the anticancer agent Sulforaphane
Journal of Agricultural and Food Chemistry, 2006Co-Authors: Nathan V Matusheski, Richard Mithen, John A Juvik, Ranjan Swarup, Malcolm J Bennett, Elizabeth H JefferyAbstract:In some cruciferous plants, epithiospecifier protein (ESP) directs myrosinase (EC 3.2.3.1)-catalyzed hydrolysis of alkenyl glucosinolates toward epithionitrile formation. Here, for the first time, we show that ESP activity is negatively correlated with the extent of formation of the health-promoting phytochemical Sulforaphane in broccoli (Brassica oleracea L. ssp. italica). A 43 kDa protein with ESP activity and sequence homology to the ESP of Arabidopsis thaliana was cloned from the broccoli cv. Packman and expressed in Escherichia coli. In a model system, the recombinant protein not only directed myrosinase-dependent metabolism of the alkenyl glucosinolate epi-progoitrin [(2S)-2-hydroxy-3-butenyl glucosinolate] toward formation of an epithionitrile but also directed myrosinase-dependent hydrolysis of the glucosinolate glucoraphanin [4-(methylsulfinyl)butyl glucosinolate] to form Sulforaphane nitrile, in place of the isothiocyanate Sulforaphane. The importance of this finding is that, whereas Sulforaphane has been shown to have anticarcinogenic properties, Sulforaphane nitrile has not. Genetic manipulation designed to attenuate or eliminate expression of ESP in broccoli could increase the fractional conversion of glucoraphanin to Sulforaphane, enhancing potential health benefits.
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heating decreases epithiospecifier protein activity and increases Sulforaphane formation in broccoli
Phytochemistry, 2004Co-Authors: Nathan V Matusheski, John A Juvik, Elizabeth H JefferyAbstract:Sulforaphane, an isothiocyanate from broccoli, is one of the most potent food-derived anticarcinogens. This compound is not present in the intact vegetable, rather it is formed from its glucosinolate precursor, glucoraphanin, by the action of myrosinase, a thioglucosidase enzyme, when broccoli tissue is crushed or chewed. However, a number of studies have demonstrated that Sulforaphane yield from glucoraphanin is low, and that a non-bioactive nitrile analog, Sulforaphane nitrile, is the primary hydrolysis product when plant tissue is crushed at room temperature. Recent evidence suggests that in Arabidopsis, nitrile formation from glucosinolates is controlled by a heat-sensitive protein, epithiospecifier protein (ESP), a non-catalytic cofactor of myrosinase. Our objectives were to examine the effects of heating broccoli florets and sprouts on Sulforaphane and Sulforaphane nitrile formation, to determine if broccoli contains ESP activity, then to correlate heat-dependent changes in ESP activity, Sulforaphane content and bioactivity, as measured by induction of the phase II detoxification enzyme quinone reductase (QR) in cell culture. Heating fresh broccoli florets or broccoli sprouts to 60 °C prior to homogenization simultaneously increased Sulforaphane formation and decreased Sulforaphane nitrile formation. A significant loss of ESP activity paralleled the decrease in Sulforaphane nitrile formation. Heating to 70 °C and above decreased the formation of both products in broccoli florets, but not in broccoli sprouts. The induction of QR in cultured mouse hepatoma Hepa lclc7 cells paralleled increases in Sulforaphane formation.
Yujuan Shan - One of the best experts on this subject based on the ideXlab platform.
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epithelial mesenchymal transition a novel target of Sulforaphane via cox 2 mmp2 9 snail zeb1 and mir 200c zeb1 pathways in human bladder cancer cells
Journal of Nutritional Biochemistry, 2013Co-Authors: Yongping Bao, Yujuan Shan, Lanwei Zhang, Mingming Gao, Xue Feng, Xiaohong Zhang, Shuran WangAbstract:Metastasis and recurrence of bladder cancer are the main reasons for its poor prognosis and high mortality rates. Because of its biological activity and high metabolic accumulation in urine, Sulforaphane, a phytochemical exclusively occurring in cruciferous vegetables, has a powerful and specific potential for preventing bladder cancer. In this paper, Sulforaphane is shown to significantly suppress a variety of biochemical pathways including the attachment, invasion, migration and chemotaxis motion in malignant transitional bladder cancer T24 cells. Transfection with cyclooxygenase-2 (COX-2) overexpression plasmid largely abolished inhibition of MMP2/9 expression as well as cell invasive capability by Sulforaphane. Moreover, Sulforaphane inhibited the epithelial-to-mesenchymal transition (EMT) process which underlies tumor cell invasion and migration mediated by E-cadherin induction through reducing transcriptional repressors, such as ZEB1 and Snail. Under conditions of over-expression of COX-2 and/or MMP2/9, Sulforaphane was still able to induce E-cadherin or reduce Snail/ZEB1 expression, suggesting that additional pathways might be involved. Further studies indicated that miR-200c played a role in the regulation of E-cadherin via the ZEB1 repressor but not by the Snail repressor. In conclusion, the EMT and two recognized signaling pathways (COX-2/MMP2,9/ ZEB1, Snail and miR-200c/ZEB1) are all targets for Sulforaphane. This study indicated that Sulforaphane may possess therapeutic potential in preventing recurrence of human bladder cancer.
